Реакция #4241

Уравнение реакции

2-(chloromethyl)benzenesulfonamide

butyl isocyanate

→

white solid

Выход 74.8%

2-(Chloromethyl)-N-(butylaminocarbonyl)benzenesulfonamide

Выход 74.8%

Растворители

xylene

Условия реакции

Обработка

1. 1
   Температураheated
2. 2
   Температураto reflux for 5.0 hrs
3. 3
   ДругоеVolatiles were removed under vacuum
4. 4
   workup.ADDITIONthe residue was treated with 0.5N NaOH (200 ml)
5. 5
   Экстракцияextracted with ethyl acetate (75 ml)
6. 6
   ДругоеThe aqueous layer was separated
7. 7
   Температураchilled
8. 8
   Экстракцияextracted with ethyl acetate
9. 9
   ПромывкаThe organic layer was washed with brine
10. 10
    Сушкаdried (MgSO4)
11. 11
    Другоеevaporated

Методика

A mixture of 2-(chloromethyl)benzenesulfonamide (13.2 g, 64 mmol) and butyl isocyanate (7.0 g, 71 mmol) in xylene (80 ml) was contacted with diazabicyclo[2.2.2]octane (0.25 g) and heated to reflux for 5.0 hrs. Volatiles were removed under vacuum and the residue was treated with 0.5N NaOH (200 ml) and extracted with ethyl acetate (75 ml). The aqueous layer was separated, chilled, acidified (pH 4) with hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and evaporated to give 14.6 g of white solid. A sample was recrystallized from toluene to give m.p. 104°-106°.

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